Awesome Q. Believe it or not, this is a pretty crowded industry with a lot of legacy solutions that have massive marketing budgets. I knew that I couldn't compete with them on a dollar per dollar basis trying to buy clicks through adwords and marketing towards managers, so I haven't bothered to go down that route... yet. Instead I have been playing to UpKeep's strengths. We created a tool for technicians and have a beautiful easy to use mobile application to go with that. So... We've been trying to drive all of our traffic to our mobile applications and encourage bottom-up adoption (technicians tell their boss there's this awesome new app called UpKeep! We should use it). I think marketing it this way, just out of the nature of our strategy, led us in the hands of lots of small-medium sized businesses, or smaller silos into large enterprises where they get more governance over the tools they use. We've seen a lot of successful users in the facility management space from coworking spaces, restaurant franchise owners, and smaller manufacturing groups.

A common use case for UpKeep is that someone sees a broken piece of equipment, pulls out their phone, opens up UpKeep, snaps a picture, and sends it off to the technician for repair. The technician now has a prioritized list of his/her tasks for the day and can easily follow up with requests!

In terms of how did I both build and market with a full time job... I didn't do any marketing for UpKeep in the beginning. I had the most common misconception that "If I built it people would come". In the beginning, UpKeep was a free application for everyone, and I viewed it more as a hobby as I was learning to program. It slowly started gaining popularity in the "free to use" category for business applications and it was fueled all by what a cool app that's completely free.

Now... If you ask about the transition from a free product into a paid service... I felt so so bad doing it because we actually upset a lot of users during that transition. But yeah that's a whole new story :)